Breaking routine

You wake up after a couple months and realize by and large you’ve lived the same day that whole time.

And the so-called real world will not discourage you from operating on your default settings, because the so-called real world of men and money and power hums merrily along in a pool of fear and anger and frustration and craving and worship of self. Our own present culture has harnessed these forces in ways that have yielded extraordinary wealth and comfort and personal freedom.

• David Foster Wallace

I recently had my first experience as an unemployed person (post-college). Thankfully, it was just a gap between jobs, but I was trying to soak it in and take advantage before jumping into my next employment journey. I had been helping my girlfriend move into her new apartment, and we decided to take the train from New York to Boston. I'd never been, it was St. Paddy's day, and we have a close friend in Boston. The stars were aligned, we were on the move.

I'm not a spontaneous guy. I get quite easily stressed and much prefer having things planned out, ready to go, reservations made. I love a reservation. Needless to say, I don't take trips with a couple days notice. This was a breath of fresh air. Boston was beautiful. We battled the elements a little bit on our day exploring the city, but we had great food, and I was attempting to embrace the unplanned nature of the trip.

In the spirit of spontaneity, I set out on our final day alone while my girlfriend worked in the afternoon for a walk. Just started walking from our Airbnb, random direction, no destination in mind. We were staying near Harvard so I ended up on campus and took a walk through the Harvard Art Museum (which I recommend). As the day wound down, I had an hour to kill and popped into a bar for a beer near our place.

this guy put me into a coma

The bar was pretty dead--a few people eating and a few of us at the bar. I was doomscrolling Substack (shame on me) trying to come up with ideas for this post, ironically enough. Two guys were at the bar, one bar seat in between them. They both knew the bartender on a first name basis, but not each other. It was clear they were locals, and as one beer turned into two their conversation picked up. Something about dogs, if I remember correctly. Admittedly, I was eavesdropping a bit. Curious about seeing two local guys just in the bar on a random Tuesday afternoon trading thoughts back and forth. A true, in the wild, organic conversation. Crazy stuff.

While sitting there, I realized I didn't know that I would have any place in my own life that I could do that. I don't know any bartenders or baristas on a first name basis. I don't really go anywhere to just be for an hour or two during the week. Sure, my friends and I have our favorite spots, but we always visit those places together. I don't go to places that I enjoy, alone, without a reason. It was obvious my two compatriots down the bar were there to enjoy the afternoon—I was too, but this wasn't my regular day to day life. It took a vacation for me to do this.

I got into a little spiral about this realization. It felt like my days had become this list of things to get done as quickly as I could. Each time block carefully crafted in my calendar, no gaps. So little room for a stop into a lunch spot to just have lunch. Had I fallen victim to the incessant productivity and life-hacking content that plagues my online algorithm? My "breaks" in the day had transformed into times for exercise, for additional studying, squeezing more out of the workday. My day didn’t feel like a unit of time in my life to soak up, but a checklist to complete as efficiently as possible.

The random trips—whether they're a long weekend or an hour trip to the local cafe or bar—cause the revelations. They spark the new ideas, the fresh perspectives. They pull you out of the routine. Believe me, I like routine as much as (probably more than) the next guy. Long stretches out of my routine really begin to weigh on me. But, if you never break it, the routine gradually entrenches itself and with every passing day it grows harder to view your days with an outside perspective (you should listen to David Foster Wallace's beautiful commencement speech on this idea, "This Is Water" quoted above). You wake up after a couple months and realize by and large you’ve lived the same day that whole time.

Everything is a spectrum. Here’s to moving a little further from the stack of productivity hacks and a little more towards the two guys at the bar.

Thanks for reading—have a great week.

The competition for our clicks, attention, and time has never been fiercer. More apps, more news, more of everything. Big Tech has centralized the web, commoditizing our screen time and dictating how we consume information. As our online selves continue to age, how do we ensure we’re truly tuned in—not just absorbing, but thinking critically?

Relay is a collective effort to distill information across tech, politics, and culture. It stands in direct opposition to the hollow drift toward cheap consumption, regrettable minutes, empty engagement, and a distorted understanding of the real world. It’s a refusal to let algorithms erode our ability to think critically—and an invitation to participate meaningfully, despite apathy becoming the social norm.

We’re focused on more signal, less noise. Tag along (it’s free).